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Chiral Phosphoric Acid‐Catalyzed Enantioselective Aza‐Friedel–Crafts Alkylation of Indoles with γ‐Hydroxy‐γ‐lactams
Author(s) -
Courant Thibaut,
Kumarn Sirirat,
He Long,
Retailleau Pascal,
Masson Géraldine
Publication year - 2013
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201201008
Subject(s) - enantioselective synthesis , phosphoric acid , chemistry , friedel–crafts reaction , catalysis , alkylation , organocatalysis , organic chemistry , combinatorial chemistry
An enantioselective aza‐Friedel–Crafts reaction of indoles with γ‐hydroxy‐γ‐lactams using a chiral phosphoric acid catalyst is reported. The approach described herein provides an efficient access to 5‐indolylpyrrolidinones in good to quantitative yields and excellent enantioselectivities (up to >99% ee ). The results suggest that the reaction may proceed via N ‐acyliminium intermediates associated with the chiral phosphoric acid anion.